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Details

Stereochemistry ACHIRAL
Molecular Formula CH5AsO3
Molecular Weight 139.9702
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLARSONIC ACID

SMILES

C[As](O)(O)=O

InChI

InChIKey=QYPPRTNMGCREIM-UHFFFAOYSA-N
InChI=1S/CH5AsO3/c1-2(3,4)5/h1H3,(H2,3,4,5)

HIDE SMILES / InChI

Molecular Formula CH5AsO3
Molecular Weight 139.9702
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Methylarsonic acid, monosodium salt is an organoarsenic compound formed from the methylation of inorganic arsenic by living organisms. Methylarsonate is used as a contact herbicide in either the monosodium or disodium salt form. It goes by the trade names Weed-E-Rad, Ansar 170 H.C., Ansar 529 H.C., DiTac and others. Methylarsonate is considered only slightly toxic, having an oral LD50 of 2200 mg/Kg for rats. The inhalation risk is greater with LD50 Rats >20 mg. Long term studies with people exposed to organoarsenicals has shown an increased risk of skin cancer (Spiewak, 2001), lung cancer and some liver cancers, although some recent studies have shown some arsenic containing compounds (specifically Arsine trioxide) may have anticarcinogenic properties (Wang, 2001). In mammals, Methylarsonate is also an intermediate in the detoxification of inorganic arsenic. In the arsenate detoxification I pathway, arsenite reacts with S-adenosyl-L-methionine to produce methylarsonate and S-adenosyl-L-homocysteine. Arsenite methyltransferase catalyzes this reaction. Methylarsonate then reacts with 2 glutathione molecules to produce glutathione disulfide and methylarsonite. This reaction is catalyzed by methylarsonate reductase. Methylarsonate is an organic arsenic compound with adverse effects similar to those of arsenic trioxide. Methylarsonate was formerly included in some vitamin and mineral preparations. It was once used to treat tuberculosis, chorea, and other affections in which the cacodylates were used.

Approval Year

PubMed

PubMed

TitleDatePubMed
Chronic exposure to methylated arsenicals stimulates arsenic excretion pathways and induces arsenic tolerance in rat liver cells.
2006 May
A pathway-based analysis of urinary arsenic metabolites and skin lesions.
2011 Apr 1
Alternative splicing variants of human arsenic (+3 oxidation state) methyltransferase.
2011 Nov 11
Methylation of arsenic by recombinant human wild-type arsenic (+3 oxidation state) methyltransferase and its methionine 287 threonine (M287T) polymorph: Role of glutathione.
2012 Oct 1
Evaluation of gene expression changes in human primary uroepithelial cells following 24-hr exposures to inorganic arsenic and its methylated metabolites.
2013 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Methylarsonate is considered only slightly toxic, having an oral LD50 of 2200 mg/Kg for rats.
Route of Administration: Oral
Arsenate and arsenic trioxide (As(2) O(3) ) inhibited the proliferation of A375 and B16F10 cells significantly at concentration ranges of 0.1-20ug/ml (P<0.001), while the organic compounds arsenobetaine, arsenocholine, dimethylarsinic acid, methylarsonic acid, tetramethylarsonium and trimethylarsine oxide did not show any inhibitory effects even at 20ug/ml.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:04:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:04:51 GMT 2023
Record UNII
J37VJ5709S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLARSONIC ACID
HSDB   ISO  
Systematic Name English
MONOMETHYLARSONIC ACID (SEE METHYLARSONIC ACID) [IARC]
Common Name English
Methanearsonic acid [WHO-DD]
Common Name English
METHYLARSINIC ACID
Systematic Name English
METHANEARSONIC ACID
MI   WHO-DD  
Systematic Name English
METHYLARSONIC ACID [IARC]
Common Name English
METHYLARSONIC ACID [ISO]
Common Name English
METHANEARSONIC ACID [MI]
Common Name English
METHYLARSONIC ACID [HSDB]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 628876
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
EPA PESTICIDE CODE 128876
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
Code System Code Type Description
CAS
124-58-3
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
MESH
C020300
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
SMS_ID
100000076530
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
HSDB
845
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
EVMPD
SUB14533MIG
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
MERCK INDEX
m7295
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY Merck Index
FDA UNII
J37VJ5709S
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-705-6
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
WIKIPEDIA
Methylarsonic acid
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
CHEBI
29852
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
PUBCHEM
8948
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID4020903
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
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SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY